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Holiday rentals in Pistakee Highlands

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Top-rated holiday rentals in Pistakee Highlands

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Cottage in Trevor
4.98 out of 5 average rating, 141 reviews

The Lakehouse-3bdr/Lakefront/Wi-Fi

Enjoy your stay at this cozy cottage just steps away from beautiful Cross Lake and 5 minutes from Antioch, IL. This 3bdr, 1bath house features a 4 seasons porch so you can relax and unwind all year. Our large yard provides ample space to enjoy the stunning view. From May-Sept 30th, you will also have access to our shared pier. Enjoy swimming, boating, fishing or other nearby activities: skiing, golfing and ziplining. Beach chairs/toys, fire pit, grill, games and folding chairs are also provided.

Guest favourite
A spacious outdoor patio features a wooden dining table surrounded by six matching chairs. Two colorful kayaks are mounted on the wall, while a private dock extends into the water, providing access for boating and fishing.
Home in McHenry
4.86 out of 5 average rating, 37 reviews

Waterfront House, 2 kayaks, Game room, Fire pit, B

Escape to this stunning waterfront house in McHenry, Illinois, offering a perfect blend of relaxation and adventure. Enjoy kayaking on the waterway leading to Pistakee Lake, fishing from the private dock, or simply unwind in the hammock. This home features a sunroom with water views, a game room for entertainment, and a cozy fireplace. With a fully equipped kitchen, outdoor seating, and a BBQ grill, it's ideal for families and groups seeking both outdoor activities and comfortable and relaxing

Top guest favourite
A cozy seating area is presented with two sofas adorned with decorative pillows. A large lamp with a blue shade complements the space, while light filters through the large windows, enhancing the bright atmosphere. A piece of wall art and natural accents are also visible.
Home in Salem
4.94 out of 5 average rating, 121 reviews

Center Lake View Cottage, near Camp&Silver Lakes

Relax & enjoy your stay in this peaceful home in quiet, friendly neighborhood. Launch boat in Center Lake at end of street or several nearby lakes. Camp Lake is 2 mins away, close to Silver Lake and many others. This home has an awesome sled hill, fire pit with seating area, and a relaxing deck with lake views. Close to Lake Geneva, & Renaissance Faire. Ski at Alpine Valley or Wilmot Mountain. 25 mins to Six Flags or Lake Geneva, 1 hr to Chgo or Milwaukee. 35 mins to Great Lakes Naval Base.

Top guest favourite
Flat in McHenry
5 out of 5 average rating, 179 reviews

Walk to downtown McHenry. Heart of the Fox River

NO PETS Entire 2nd. floor. < 2 blocks away from downtown, Fox River Riverwalk. Pokémon Gym across the street. Full stocked kitchen, books, games, toys & extra amenities to make your stay beyond relaxing. 4:20 allowed in backyard & not in view of under the age of 21. Private smoking area in front. Minutes from 2 State Parks, 1 with free boat/kayak launch. Several marinas, boat rentals, golf courses & other varieties of entertainment. Look at Bettye's Guidebook for more information.

Superhost
A tranquil evening scene showcases a hot tub on the deck, with two glasses positioned on the edge. The vibrant sunset casts warm colors over the lake, reflecting off the water where a pier extends into the distance. Soft grassy areas are visible in the foreground.
Home in Ingleside
4.87 out of 5 average rating, 167 reviews

Chain O' Lakes Nautical 2/2 Lake House w/ Hot Tub

Welcome aboard First Mate’s Retreat! Unique and cute 2 bed / 2 bath nautical lake house has the best views of the Chain O' Lakes. Be amazed on the walk out lake view wood deck in the back yard, and watch sunsets fall over the bay and color the sky. The back patio is a great place to relax, entertain & relax. Fish or dock your watercraft at our pier if needed. There is a 4-5 person hot tub on the back deck for you to relax and unwind (Hot tub included in the price on this property).

Top guest favourite
A spacious living area is highlighted by large windows offering views of the water. Colorful seating options, including bean bags and patterned chairs, complement a wooden coffee table. Sleek ceiling fixtures and a soft rug define the gathering space, enhancing the open layout.
Home in Richmond
4.96 out of 5 average rating, 228 reviews

TheGlassCabin@HackmatackRetreat

The Pond House, a vintage glass cabin filled with art, water views & eclectic vibes privately perched on the sacred grounds of Hackmatack Retreat Center. Native prairie, a winding slow river, two ponds, 200+ year old oaks & big sky- Countless places to curl up, gathering, focus-- nooks and crannies indoors and out, we offer “time out for time in” amidst this noisy world. Minutes from 2 small towns, all amenities, we're all about peace & ease-- let us custom curate your experience !

Top guest favourite
A historic stone home built in 1911 is prominently featured, showcasing its grand architectural details. The façade includes a porch supported by strong columns. A group of individuals stands in front, illustrating the home's welcoming presence in its early days amidst a natural landscape.
Guest house in McHenry
4.96 out of 5 average rating, 202 reviews

"The Apartment" in the heart of downtown McHenry

We welcome you to be our guest in this charming, historic home built in 1911 by a German mason. This upper unit Apartment is a spacious 1,100 square feet, lovingly restored with a vintage aesthetic in 2018. The private entrance to "The Apartment" will lead you to; 2 cozy bedrooms & 1 vintage inspired yet modern bath with walk in shower. A large living room, dining area and bright clean kitchen will make you feel right at home. 9 foot ceilings and tons of natural light through out.

Guest favourite
Home in Fox Lake
4.9 out of 5 average rating, 162 reviews

Spacious Lakefront Retreat | Sunset VIEW | Firepit

Welcome to Howard House by Evereste Experiences. A hidden gem on the Fox Chain o' Lakes. Situated centrally on the lakefront of beautiful Nippersink Lake just an hour outside of Chicago, this spacious and stylish retreat is located on a hill with ultimate views of the lake and stunning sunsets over the water. Located near downtown Fox Lake and the Metra train stop. With a large back deck, over 60ft of lake frontage, a dock, firepit and swimming area, you'll never want to leave!

Top guest favourite
A serene living area features a large sliding glass door leading to a deck with unobstructed views of Round Lake. Natural wood accents adorn the wall, while a plush sofa and a small coffee table create a relaxing seating space.
Home in Round Lake Beach
4.99 out of 5 average rating, 199 reviews

Round Lake Getaway Retreat

Looking for a calming, peaceful lakeside getaway for you and your loved one? Come stay at our remodeled retreat with private waterfront access to Round Lake. Enjoy peace and reflection meditating on the spirited lake waters rolling into shore. Wake up to inspirational lake views with soul warming coffee, tea or cocoa. Savor deep or lazy conversation with your loved one, surrounded by dreamy décor and captivating nature. Come and relax, restore, and rejuvenate by the lake!

Top guest favourite
A grassy area features multiple wooden lounge chairs facing the lake. A small fire pit is positioned in the center. Behind, a light-colored shed and a dock can be seen, with boats and kayaks stored nearby. A vibrant sky with colorful clouds adds to the scene.
Home in Fox Lake
5 out of 5 average rating, 108 reviews

Wonderful Mineola Bay Lakefront Cottage 4adu+4kids

Book a romantic weekend or bring the whole family to this cozy, clean and well-appointed lake house that has plenty of room for fun. Embrace lake-life at its finest when you call this Fox Lake cottage on Mineola Bay your home away from home! We have a dock to park your boat, so bring it. Access to restaurants, bars, convenience and grocery stores, boat launches and more. Or hang out and soak in the sunshine while paddle boarding, boating, kayaking, swimming and nature hikes.

Guest favourite
A modern house features an inviting front porch with landscaped gravel beds and well-maintained grass. A wooden garage door complements the green exterior walls. Surrounding trees and shrubs enhance the outdoor space, creating a welcoming entrance.
Home in Twin Lakes
4.98 out of 5 average rating, 126 reviews

4Bd 3.5ba Cozy New Construction! Close to lake!

Welcome to our cozy home! Twin Lakes is quintessential small town America situated surrounding lakes Elizabeth and Mary in Wisconsin. Less than 15 minutes from downtown Lake Geneva and less than 5 minutes from Richmond, Illinois. During your stay you can experience much of what the area has to offer including boating and fishing on Lakes Elizabeth and Mary, access to the community beach, local shopping, and peaceful country nights in this small family-oriented community.

Guest favourite
An inviting entrance to the cottage is shown, featuring a small wooden deck with two folding chairs and a table. Steps lead to a white door framed by white siding, while greenery adds a natural aesthetic to the pathway.
Home in Fox Lake
4.92 out of 5 average rating, 24 reviews

Lakeside Getaway 1 Bedroom

Take a break and unwind at this peaceful oasis. The holiday home features lake views, air-conditioning, and a fully equipped kitchen with a refrigerator, microwave, dishwasher, oven, and stovetop. Additional amenities include a dining area, TV, and outdoor dining space. Not far from Chicago O'Hare International Airport (36 mi), Six Flags Great America (14 mi), Naval Training Center, Great Lakes (22 mi), and Raging Buffalo Snowboard Ski Park (23 mi).

Popular amenities for Pistakee Highlands holiday rentals